Synthetic study demonstrates chemoselective synthesis of benzofuro[3,2-d]pyrimidin-2-amines from azadienes, indicating an exclusive pathway through carbodiimide anion intermediates.
The chemoselective [4+2] annulation/aromatization reactions between benzofuran‐derived azadienes and N‐Ts cyanamides are developed, affording a convenient method for synthesizing benzofuro[3,2‐d]pyrimidin‐2‐amines under mild conditions. Herein, N‐Ts cyanamides selectively participated in reactions absolutely via carbodiimide anion intermediates and the corresponding cyanamide anion intermediates derived products were not observed. The proposed chemoselective stepwise reaction mechanism was well supported by DFT calculations.
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Wang et al. (2024) studied this question.
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